Ranking Tottenham's 10 best transfer windows of the Premier League era | OneFootball

Highlights

Tottenham Hotspur have long been regarded as an ambitious club who are always in the top-four conversation and have even challenged for club football's most elite prizes. As part of that seemingly endless pursuit of glory, they have spent a lot of money trying to bolster that squad.

Daniel Levy has served as the club chairman since 2001 and has garnered something of a reputation for his ability to drive a hard bargain, During his reign, the club have signed plenty of top players who have gone on to enjoy a lot of success with the North London outfit. The likes of Christian Eriksen, Heung-min Son and Dele Alli, who all played a major role in Spurs reaching the Champions League final in 2019 immediately spring to mind as examples.

Here at GIVEMESPORT, we've ranked their ten greatest transfer windows of the Premier League era. The concept of a transfer window was only introduced to the division in 2002, so any business conducted before then has not been considered for this list.

Ranking factors

This list has been determined based on several aspects:

Some of these signings immediately improved the squad they joined, whereas others took a while to come good but as long as they enjoyed a successful spell with the club or were sold for a major profit, they would boost the window in which they were signed. Similarly, any players who were sold at the right time and for the right price will also help the credentials of the window in which they departed and if they helped the club generate a net profit across that window, that's only a bonus.

It must also be noted that individual signings will not always outweigh the business that goes alongside them. For example, Luka Modric was an excellent signing for Tottenham in 2008 and was sold for a major profit four years later, but the rest of Spurs' business that summer denies that window a place on this list.

10 2004/05 summer window

Tottenham conducted a lot of business during the summer of 2004. Their most notable acquisition was that of Michael Carrick from West Ham United for just £3.5m which, given the fact he would join Manchester United for £14m just two years later, was a remarkable deal.

The signing of England's number one Paul Robinson from Leeds United for a mere £1.4m was also good business and the shot-stopper would make 175 appearances in four years at White Hart Lane. However, the rest of their additions left a lot to be desired, with none of them staying at the club for more than three years, and they prevented this window from being ranked any higher.

9 2007/08 winter window

It was in the 2007/08 season that Spurs last won a major trophy, with a shock 2-1 win over Chelsea in the League Cup final. They made three major signings in the summer to help them achieve that goal, including making their most expensive ever purchase at £16.5m.

That price tag was attributed to Charlton Athletic's Darren Bent, who would score 25 goals across two seasons with the club, and he arrived alongside defender Younes Kaboul and talented £5m-rated youngster Gareth Bale, who took a while to get going but would eventually become the most expensive player in world football. To top it off, Tottenham also managed to raise £6m from the sale of out-of-sorts forward Mido to Middlesbrough.

8 2014/15 winter window

This window makes it in purely for the signing of Dele Alli. The attacking midfielder had been making waves at MK Dons which prompted Spurs to spend £5m to sign him in the January window, before loaning him back to the League One side for the rest of the season where he continued to excel.

Once he returned, he was ready to tear up the Premier League despite his tender age of 19, and he would prove a key player as Spurs challenged for the title in the next two seasons and reached the Champions League final in 2019, before issues off the pitch somewhat derailed his career and he ended up joining Everton on a free transfer, with instalments added should he recover his form, in 2022. Despite this inauspicious end to life at Tottenham, he remains a beloved figure in that part of North London, having scored 67 goals in 269 appearances during his time at the club.

7 2009/10 summer window

The 2009/10 window was Harry Redknapp's first summer window as Tottenham manager and he immediately went to his old club Portsmouth, who were desperately offloading players as they tried to avoid slipping into financial abyss. Peter Crouch was signed for £10m and would go on to score the goal that confirmed Tottenham's place in Europe's elite competition for the first time in almost 50 years, and Niko Kranjcar was also added for £2.5m.

Sebastien Bassong was also snapped up from relegated Newcastle United for £8m but didn't quite have the desired impact and was sold for a considerably smaller fee three years later, while youngster Kyle Walker was a signing who would come good later down the line. Spurs also sold several players including Darren Bent, Didier Zokora and Kevin-Prince Boateng which almost saw them break even across the window.

The winter of 2022 saw Tottenham make two very astute additions to their squad from Juventus. Rodrigo Bentancur was snapped up for £15.86m and would be a crucial asset for Antonio Conte's team for the remainder of the season and the next before suffering an unfortunate Anterior Cruciate Ligament injury in a match against Leicester City in February 2023.

Talented right winger Dejan Kulusevski followed his teammate from Turin to North London and he completed a devastating front three consisting of himself, Heung-min Son and Harry Kane. The Swede was signed on an 18-month loan deal and bagged seven goals and 18 assists during this time before the move became permanent in the summer of 2023.

5 2023/24 summer window

We're going to give Ange Postecoglou the benefit of the doubt and say he's done well in his first transfer window as Tottenham manager. The inevitable sale of Harry Kane, who joined Bayern Munich for an estimated £87m was always going to make things difficult, but on the whole, Spurs were able to cope pretty well.

The signing of James Maddison from Leicester City for £40m has already proven to be a success with three goals and five assists in his first 11 matches as a Spurs player. Empoli goalkeeper Guglielmo Vicario looks like a snip at £16.5m and the signings of Brennan Johnson and Mickey van de Ven as well as making Pedro Porro's deal permanent all showed consideration for the future and all three players appeared to have slipped seamlessly into the type of system the Australian wants to deploy.

4 2010/11 summer window

Tottenham had a very successful summer in 2010 as they prepared for their very first Champions League campaign. Having fallen out of favour at Real Madrid, Spurs were able to sign attacking midfielder Rafael van der Vaart for just £8m and the Dutchman ended the season as the club's top scorer with 15 goals in all competitions.

Internacional defensive midfielder Sandro, who by that time was a full Brazilian international, was also added to the team for the same price, and he would be a regular in the team for the next few seasons. William Gallas was also brought in on a free transfer, providing some much-needed continental experience as well as infuriating Arsenal supporters.

3 2022/23 summer window

Because a difficult campaign followed in which Tottenham slumped to eighth place in the table under Antonio Conte, it wouldn't become apparent until much later just how well the club had done in the 2022 summer window. The likes of Yves Bissouma and Destiny Udogie were either used incorrectly or not played at all by the Italian, but would become vital cogs within Ange Postecoglou's team the following season and only cost Spurs a combined £40m.

Cristiano Romero was also brought in permanently and within a few months would be winning the World Cup with Argentina while Richarlison still hasn't quite hit the ground running, he is unquestionably playing with more freedom under Postecoglou and seems to have more of a role to fulfil now Kane has left. In addition, Spurs did very well to all but recoup the money spent on Steven Bergwijn when they sold him to Ajax for £26.4m.

2 2015/16 winter window

This was the summer that saw Tottenham transform from Champions League hopefuls into title challengers. In Mauricio Pochettino's second season in charge, the club were incredibly able to generate a net profit across the window as the Argentinian made two very astute additions to his squad in Toby Alderweireld and Heung-min Son.

Commanding centre-back Toby Alderweireld would go on to make 236 appearances in five years in North London after arriving from Atletico Madrid for just £11.4m, while Heung-min Son's arrival from Bayer Leverkusen for £22m gave Spurs a whole new dimension up top as the South Korean proved to be the perfect foil for talisman Harry Kane. The club also brought in Kieran Trippier, who, despite never truly living up to his potential at White Hart Lane, would end up being sold for a major profit four years down the line.

1 2011/12 summer window

The window Daniel Levy will surely be most proud of in his time as Tottenham chairman came in the summer of 2011 when Spurs generated a handsome net profit while simultaneously strengthening their squad. After winning FWA Player of the Year with relegated West Ham the year before, the £5.5m-rated Scott Parker was the only signing who cost any money and he would end up in the PFA Team of the Year that season.

Brad Friedel was signed on a free transfer from Aston Villa and proved a reliable presence between the sticks despite being 40 years old, while Emmanuel Adebayor joined on a season-long loan from Manchester City and scored 17 league goals in the 2011/12 season, including a penalty against former club Arsenal in the North London derby. Spurs sold several surplus players including Peter Crouch, Wilson Palacios and Jamie O'Hara to ensure they made money that summer.